Carbon Disulfide → (3S)-2-[(2-Thenylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

HRID 1249050Notes

Reaction equation

HRID 1249050 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@@H:3]([C:14]([OH:16])=[O:15])[NH:2]1.[OH-].[K+].[C:19](=[S:21])=[S:20].[C:22]1([CH2:27]Cl)[S:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[C:22]1([CH2:27][S:20][C:19]([N:2]2[C@H:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:12][C:13]=3[CH2:1]2)=[S:21])[S:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 698302-(Chloromethyl)thiopheneHCID 449440(3S)-1H,2H,3H,4H,9H-pyrido(3,4-b)indole-3-carboxylic acid

Product 1

HCID 13561951(3S)-2-[(2-Thenylthio)thiocarbonyl]-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same manner as descsribed in Example 32, (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (4.33 g), KOH (2.33 g), carbon disulfide (1.22 ml), 50% ethanol (80 ml) and 2-thenyl chloride (3.1 g) are reacted and treated to give the title compound (3.15 g) as pale yellow powder.

Workup

  1. customare reacted
  2. additiontreated

Sources & evidence

ORD record
ord-f348eaa2c3184b9e91e3045572b277be
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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